Adducts of quinone compounds and amine-containing polymers for use in lubricating oils and in fuels

Abstract

Adducts useful as fuel or lubricating oil additives are disclosed. The adducts comprise the reaction product of at least one quinone compound and an amine-containing polymeric material comprising at least one member selected from the group consisting of (i) a first amine-containing polymer derived from a hydrocarbon polymer having a number average molecular weight of from about 300 to 20,000 and (ii) a second amine-containing polymer having a carbon-carbon backbone and formed by the process of polymerizing an organometallic compound-masked nitrogen containing monomer and a polymer chain monomer selected from the group consisting of ethylene, C 3 to C 25 alpha-olefins, and mixtures thereof, followed by deashing to remove the organometallic compound; wherein the amine-containing polymeric material has within its structure at least one reactive amino group selected from the group consisting of primary amino groups, secondary amino groups and mixtures thereof. The adducts possess dispersant, detergent, antioxidant and anti-corrosion properties.

What is claimed is: 
     
       1. An oil soluble adduct useful as a fuel additive or lubricating oil additive comprising the reaction product of: at least one quinone compound having at least one hydrogen on the quinone ring; and   an amine-containing polymer having within its structure at least one reactive amino group selected from the group consisting of primary amino groups, secondary amino groups and mixtures thereof, the amine-containing polymer being derived from a hydrocarbon polymer having a number average molecular weight of from about 700 to 15,000, the amine-containing polymer comprising the acylated amine reaction product of hydrocarbon polymer-substituted mono- or dicarboxylic acid producing material and an amine compound containing at least two reactive amino groups selected from the group consisting of primary amino groups, secondary amino groups, and mixtures thereof.   
     
     
       2. The adduct according to claim 1, wherein the hydrocarbon polymer-substituted mono- or dicarboxylic acid producing material is formed by reaction of the hydrocarbon polymer with a monounsaturated carboxylic reactant selected from the group consisting of a monounsaturated monocarboxylic acid producing compound, a monounsaturated dicarboxylic acid producing compound, and mixtures thereof. 
     
     
       3. The adduct according to claim 1, wherein the hydrocarbon polymer-substituted mono- or dicarboxylic acid producing material comprises a Koch functionalized polymer formed by the reaction of carbon monoxide, a nucleophilic trapping agent, and the hydrocarbon polymer; wherein the hydrocarbon polymer contains polymer chains having at least one carbon-carbon double bond. 
     
     
       4. The adduct according to claim 1, wherein the hydrocarbon polymer is selected from the group consisting of alpha-olefin homopolymers, alpha-olefin copolymers, ethylene-alpha-olefin copolymers, and mixtures thereof. 
     
     
       5. The adduct according to claim 4, wherein the hydrocarbon polymer comprises ethylene-alpha-olefin copolymer derived from ethylene and at least one C 3  to C 28  alpha-olefin having the formula H 2  C═CHR', wherein R' is a straight or branched chain alkyl radical comprising 1 to 26 carbon atoms, the ethylene-alpha-olefin copolymer having an ethylene content of about 20 to 80 mole percent, and wherein at least about 30 percent of the polymer chains possess terminal ethenylidene unsaturation. 
     
     
       6. The adduct according to claim 1, wherein the hydrocarbon polymer comprises a member selected from the group consisting of polybutene and polyisobutylene. 
     
     
       7. The adduct according to claim 1, wherein the quinone compound is selected from the group consisting of 1,4-benzoquinone and 1,4-naphthoquinone. 
     
     
       8. A lubricating oil composition containing from about 0.01 to 20 weight percent of the adduct of claim 1. 
     
     
       9. A lubricating oil concentrate containing from about 20 to 60 weight percent of the adduct of claim 1. 
     
     
       10. A fuel composition containing from about 0.001 to 0.5 weight percent of the adduct of claim 1. 
     
     
       11. The adduct according to claim 1, wherein the amine compound comprises a polyalkylene polyamine having about 2 to 60 carbon atoms and about 2 to 12 nitrogen atoms per molecule. 
     
     
       12. The adduct according to claim 2, wherein the monounsaturated carboxylic reactant comprises maleic anhydride. 
     
     
       13. The adduct according to claim 12, wherein the hydrocarbon polymer comprises a member selected from the group consisting of polybutene and polyisobutylene. 
     
     
       14. The adduct according to claim 3, wherein the Koch functionalized polymer contains acyl functional groups of formula: ##STR11## attached to a carbon atom of the hydrocarbon polymer backbone, wherein Y is O or S; and R 5  is substituted hydrocarbyl, aryl, or substituted aryl. 
     
     
       15. The adduct according to claim 14, wherein at least about 50 mole % of the acyl functional groups are neo. 
     
     
       16. A process for producing a composition useful as a fuel additive or lubricating oil additive comprising the steps of: providing at least one quinone compound having at least one hydrogen on the quinone ring;   providing an amine-containing polymer having within its structure at least one reactive amino group selected from the group consisting of primary amino groups, secondary amino groups and mixtures thereof, the amine-containing polymer being derived from a hydrocarbon polymer having a number average molecular weight of from about 700 to 15,000, the amine-containing polymer comprising the acylated amine reaction product of a hydrocarbon polymer-substituted mono- or dicarboxylic acid producing material and an amine compound containing at least two reactive amino groups selected from the group consisting of primary amino groups, secondary amino groups, and mixtures thereof; and   contacting the quinone compound with the amine-containing polymer under conditions and for a time sufficient to react the quinone compound with at least a portion of the reactive amino groups to form a product mixture containing an oil soluble adduct of the quinone compound and the amine-containing polymer.   
     
     
       17. The process according to claim 16, wherein the quinone compound is selected from the group consisting of 1,4-benzoquinone and 1,4-naphthoquinone. 
     
     
       18. The process according to claim 16, wherein the amine compound comprises a polyalkylene polyamine having about 2 to 60 carbon atoms and about 2 to 12 nitrogen atoms per molecule. 
     
     
       19. The process according to claim 16, wherein the hydrocarbon polymer-substituted mono- or dicarboxylic acid producing material is formed by reaction of the hydrocarbon polymer with a monounsaturated carboxylic reactant selected from the group consisting of a monounsaturated monocarboxylic acid producing compound, a monounsaturated dicarboxylic acid producing compound, and mixtures thereof. 
     
     
       20. The process according to claim 16, wherein the step of providing the quinone compound comprises contacting a dihydroxyaromatic compound with an oxidizing agent.